Organic Chemistry 2 – CHEM 322

Spencer Chemistry Building

Professor: Dr. J.R. Dias

Office: Spencer Chemistry Building, Room C106

Website: http://cas.umkc.edu/chem/dias.htm

Pre-requisite: A thorough understanding of Organic Chemistry I is needed!!!

Course Objectives: The student should evolve their understanding of organic chemistry to the level that they will be able to define most of the Key Terms on pages A1 to A20 in the text, “Organic Chemistry” by Maitland Jones, Jr..

Office Hours and Homework Assist Session: Office hours are open. The Homework Assist Session is not an officially scheduled part of the class and is done only at the benevolence of the professor. It is recommended that the student come to these sessions prepared to ask questions that cause them difficulty.

Attendance Requirement: Since there are 38 - 50 minute lectures to cover 10 chapters in a text having a total of 23 chapters in 5 weeks, it is necessary for the student to attend all of the lectures (the Homework Assist Session is not a make-up session). Expect to cover 2 chapters a week.

Exams and Quizzes: There will be a Quiz every class meeting. The 1-hour exams will be after every third chapter covered in class. The exams will be made up of questions similar to the problems in the text along with critical material from lecture. There will be no make up exams. This course will require considerable dedication of your time.

Grading: Grades will not be curved but determined numerically per the following scale: >90 %, A; >80 %, B: > 70 %, C; > 60%, D; < 50 %, F. Plus/minus will be used.

Cheating: Academic dishonesty will result in a failing grade for the course.

Homework Problems: The student should complete and understand all the text Examples and worked problems and be able to reiterate the Summaries. Do as many problems as possible!

End of Course Knowledge: The student should be able to give a specific example of each item in the following outline.

Reaction Types

Addition Reactions

a)      ionic – anti

b)      molecular – syn

c)      electrophilic

d)      nucleophilic - principally of carbonyl and nitrile

Elimination Reactions

a)      E1 – electrophilic

b)      E1cB - nucleophilic

c)      E2 – anti, base induced versus reductive induced

d)      Retro-reactions

e)      Oxidative elimination

Substitution Reactions

a)      S_N1 – electrophilic, racemization

b)      S_N2 – inversion

c)      Free-radical – chain reactions, initiation, propagation, termination

d)   Leaving groups (nucleofuges)

e)      Electrophilic aromatic – addition/elimination

f)       Nucleophilic aromatic on substituted nitrobenzene and pyridine – addition/elimination

g)       Benzyne – base induced elimination/addition

h)      Aldehydes/ketones – addition/elimination replacement of carbonyl oxygen

i)        Carboxylic acid derivatives – addition/elimination replacement X group, electrophilic or nucleophilic

j)        Benzenediazonium

Rearrangements Reactions

a)      electrophilic – 1,2-hydride and alkyl shifts

b)      nucleophilic

Miscellaneous Reactions

      a) Cleavage

Concepts

1)      Structural – constitutional isomerism, stereoisomerism (enantiomers, diasteromers, R, S, E, Z, erythro, threo, meso), conformational isomerism (eclipsed/staggered ethane, syn, anti, gauche and chair/boat subsystems, axial, equatorial), functional groups (EWG versus EDG)

2)      Energetics and driving-force – bond dissociation energies, σ-bonds are stronger than π-bonds, HOMO/LUMO, relative stability, the more substituted π-bond is more stable, the more conjugated π-bond is more stable, resonance – aromatic (4n+2 rule) and charge dispersal, Hammond’s postulate, microscopic reversibility, transition state theory, polarization factors

3)      Mechanistic – arrow formalism for electron flow, electrophilic, nucleophilic, reactive intermediates (radicals, carbocations, carbanions)